Herbicidal compositions



Fatented Sept. 1%, HQSZL MRBICIDAL CGOSHTEQNE Luther L. Baumgartner, Hastings on Hun, N. Y., assignor to The B. F. Goodrich Gompany, New York, N. Y., a corporation of New York No Drawing. Application December 10, 1948,

Serial No. 64,710

6 Claims. (Cl. 71-2.3)

This invention relates to herbicidal composiwhich can be employed to prepare the compositions and more specifically pertainsto heribicidal tions of this invention include, for example, compositions containing a chlorophenyl alkyl or methyl, ethyl, propyl, isopropyl, butyl, allyl. alkenyl carbonate as the toxic ingredient, tomethallyl, and butenyl mono-, di-, tri-, tetra-, gether with a mineral oil as carrier, and to the 5 and pentachlorophenyl carbonates. Of these, use 01' such compositions in killing weeds, and polychlorophenyl allyl carbonates and polychloroundesirable grasses and in various other herbiphenyl ethyl carbonates, are preferred for the cidal applications. preparation of the herbicidal compositions of this I have discovered that when a chlorophenyl invention.

carbonate having the formula: The mineral oil used as the carrier in the herbicidal compositions described herein may be any oil consisting predominantly of hydrocarbons j o c o preferably parafiln hydrocarbons containing from I 10 to 20 carbon atoms. Such hydrocarbons generally possess a boiling point about 150 C. and a where n is an integer from one to five, preferably Saybolt viscosity bel w 200 seconds, Examples of from 2 to 5, and where R is a hydrocarbon radical such 11 ar k r sene, diesel fuel oils, bunker C cted om th alkyl and alkenyl p is fuel oil, and other similar hydrocarbon mixtures mixed with a mineral Oil consisting Predomin whether or not derived from petroleum. In antly of hydrocarbons containing from 10 o 20 general, the lighter petroleum fractions and carbon atoms such as kerosene and fuel oils, in especially k rosen are preferably employed in concentrations as low as about 0.1% by weight, preparing spray compositions for useintemperate the resulting compositions are exceedingly efiecclimates hil the heavier higher molecular tive herbicides, being useful in killing a wide weight petroleum ils su h as the diesel fuel oils variety of weeds and grasses including varieties are t it d for formulations to be used in the which are not controlled eilectively with known tt l t herbicides- Compositions consisting entirely of the chloro- These chlorophenyl c bo t can be D phenyl carbonate in a concentration between 0.1 pared by th well known r ctions employin and 10% by weight dissolved in the carrier oil plmsgene and alcohols- For exampleby reacting may be sprayed on plants to produce the herbione mole of ethyl alcohol with one mole of phoscidal eflect, If desired, however, the chlorophenyl gene there is formed ethyl chlorocarbonate (ethyl carbonate di ol ed in the oil may be emulsified chloroformate) and hydrogen chloride according in water ith th aid of a. wetting or dispersing t0 the following reaction: agent to produce an oil-in-water emulsion con- 01-0-0] 02115011 ClCOCzHu H01 taining from 0.1 to 10% by weight of the chlorophenyl carbonate and an oil content from 1 to of that of the water. and the resulting The ethyl chlorocarbonate 15 then reacted with emulsion sprayed on plant nm In either event a chlorophenol to produce the desired chloro- I have found that the application of the phenyl ethyl carbonate and hydrogen chloride ac- 0 positions in amounts Such as to provide as little cording to the following reaction: as 1 to 10 lbs. of the chlorophenyl carbonate per acre of sprayed area is suflicient to kill a variety I of undesirable weeds and grasses although, of OH C1-C4) course, higher rates of application up to 50 lbs. of

t 5 chlorophenyl carbonate per acre may be em- Cle ployed in some instances.

The wetting or dispersing agents which can 043-0 H0] be used in preparing the oil-in-water emulsions it include those typified by the following general where n is an integer from one to five. In place classifications: sodium and g g i g of ethyl alcohol, other alkyl and alkenyl alcohols nifty aclds ,known as a; and g may be employed to produce the corresponding aclds Sapomfied with am es an i alkyl and alkenyl chlorophenyl carbonates. water'soluble g i i izg Moreover, in the second reaction, any mono-, di-, 331d known as rosin Soaps, g: F8011]; e sa tritetraor penta-chlorophenol may be em- 55 of the hydroxy a hyde acl prese oi mlsslefi ployed as well as the mixture of chlorinated a f? 9: 2 355 gf phenols which results from the chlorination of a1 a f p ter soh1b1e long chain a1c0 phenol. Hereinafter, for convenience, the prodsulfona e 10 to 18 arbon atomy uct of the reaction of an alkyl or allqrlene chloro- 1118 usually contammg c I carbonate witha mixture of the various chloro- Water-Soluble salts of fatty acld amide Wallerphenols will be referred to as mixed-chlorophenyl o u le S s of Sulfated ty a i este ralkyl or alkenyl carbonates. soluble alkyl sulfonates containing 8 to 20 car- The alkyl and alkenyl chlorophenyl carbonates bon atoms in the alkyl group; Water-soluble aryl 3 sulfonates; water-soluble alkyl aryl sulfonates; water-soluble aralkyl sulfonates; water-soluble sorbitan mono-laurates, -palmitates, -stearates, and -oleates; quaternary alkyl halides; fatty poly ethers; and others. These wetting or disp rslng agents are sold under numerous trade names and may be either pure compounds or mixtures of compounds of the same general r up- In general such wetting or dispersing agents are employed in concentrations 01' from about 0.1% by weight to about by weight based on the total weight of the composition prepared. The amount employed will vary not only with the quantity of oil to be emulsified but will vary with the efliciency of each dispersing agent to form a suitable stable oil-in-water emulsion.

When the herbicidal compositions of this invention are applied to plants, their toxic activity is manifest by difierent outward signs depending on the particular variety of plant. For example, plants with apical meristems such as stinging nettle (Urtica dioios) cease growing after application of the composition but as much as a week may elapse before the plants are completely dead. Plants of the lily family, as exemplifled by the common onion, exhibit no external symptoms of the action of the herbicide until the bulb is well rotted. Carrots and. burdock react to these herbicides by developing acute necrosis at the juncture of leaves and root stock before the plant is dead.

The following specific examples which appear in tabulated form illustrate the wide utility of the herbicidal compositions with which this invention is concerned. In each example a composition of the nature shown was sprayed on an agricultural plot in which was growing the plants indicated. Where no rate of application is given the compositions were applied to the plants as a fine mist spray until the leaves of the plants were wetted with the spray composition. All sprayed plants were killed by the application unless otherwise indicated.

TABLE I Ethyl chlorophcnyl carbonates Concentra- Example Ethyl Carbonate Employed gg b Carrier, parts by weight Plants Treated and Killed weight 2,4-dichlorophenyl 1.0 IOU-kerosene.-. Large mature burdock. igflgcrigiloroghenlyl go. beamttoigiajto, radish, buckwheat.

en orop eny o oma o, o acco ean. Mlxed-chloropbenyl 1.0 oil-in-water 5o emulsion 50.0 kerosene CrabgraSs. Mixed-c111 i1 1 1 o 1 i m ii k 5 orop eny oi n-wa r erosene em ion -w-ater 2335 2 1.0-Igepal 300 gr Mlxed-chloropbenyl 1.0 lOO-kerosene J ananese Honeysuckle. llgixetgfiloroglhenyl i.l..ido. ta- ;66 .t of all weeds in a weed plot killed. en Orop eny, apo n-wa r we on.

plied at 4.0 lbs. toxicant emulslon.--.{igaol:%ergsenlef.ido f ggg g Dams grass carpet peracre. on

1 Triton N--Tertiary octyl phenoxy polyether alcohol emulsifier. Igepal 800-Fatty polyetber emulsifier.

TABLE II Allyl chlorophenyl carbonates Concentra- Allyl Carbonate Employed Carrier, parts by weight Plants Treated and Killed 2,4,6-trichlorophenyl 2.4,6-trichlorophenyl 2,4,5-trlchloro phenyl applied at 10 lbs. oi tox- IOO-kerosene bean, tomato, radish, buckwheat. radish, bean, tomato.

radish, bean, and tomato. ragweed.

crabgrass.

Do. dock, Dallas grass, carpet grass, burr weed, spur grass.

dock, dandelion, golden rod.

complete kill of mixed weeds and grasses including Johnson grass, pepperweed and dandelion. 80% of treated wild onions killed. 9575B! treated wild onions killed.

0. crabrgass.

crabgrass, rye, dock.

icant per acre. 16 2,4,5-trichloro-phenyl 5.0 440-kerosene applied at 5 lbs. oi toxicant per acre. 17 Pentachlorophe nyl l 0 applied at 1.0 lb. per acre. 18 2,4,6-trlchlorophenyl. 10 19... do 5 20.-- pentachlorophenyl 5 2i--- mlxed-chlorophenyl 0. 22 mixed-chlorophenyl apl.

plied at 1.0 lb. per acre. sion 00 23 --do l. 0 oll-ln-water emul- ZO-kerosene. sion water 1.0 Triton Nl00 24 mixed-chlorophenyl 1.0 loo-kerosene 0.5 do 0. 25 do }dandelion, ragweed, Spanish nettle.

Triton N-100='1ertiary octyl plienoxy polyether alcohol emulsifier.

Control tests were also carried out by spraying weed plants in the same plots with kerosene containing no toxicant. In general it was found that the application of kerosene at the same rate used in the herbicidal trials had little or no effect on the plants treated.

In addition to the compositions employed in the tests of Table I and Table II mixed-chlorophenyl isopropyl carbonates were also employed to prepare herbicidal compositions. The following is an example of the toxicity of such compositions. Large mature burdock plants were sprayed with a kerosene solution containing 1% by weight of mixed-chlorophenyl isopropyl carbonate. After a few days all of the burdock Plants so treated were dead. An oil-in-water emulsion containing mixed chlorophenyl isopropyl carbonates was prepared by emulsifying 20 parts by weight of the 1% carbonate solution in this solution in 80 parts by weight of water in which was dissolved 0.5% by weight of dilauryldimethyl ammonium bromide as an emulsifying agent. This composition was sprayed on bluegrass. After 7 days all of the bluegrass so sprayed was dead.

The compositions employed in the tests of Table I and Table II as well as the above compositions containing mixed-chlorophenyl isopropyl carbonate are effective killers not only of the weeds and grasses listed but also are eifective against wheat, corn. timothy, barnyard grass, Johnson grass, yellow fox tail and cattall as well as other similar plant species. Many of the plants effectively killed with these compositions cannot be controlled with other known herbicides.

In general, the concentration of the toxic ingredient necessary for satisfactory herbicidal activity will vary with air temperature as is the case in the use of other herbicides such as 2,4- dichlorophenoxy acetic acid (2,4D) and its salts and esters. For example, where the use of a composition containing a concentration of 0.1% to 0.5% of the toxicant is satisfactory to obtain good kill of one or several species during hot weather, compositions containing 1% to 5% of the toxicant may be required during cool to cold weather to accomplish the same results.

While I have herein disclosed various embodiments of the invention, it will be understood that I do not intend that the invention be thereby limited, but only as required by thespirit and scope of the appended claims.

I claim:

1. A herbicidal composition comprising as an essential active ingredient 0.1% to 10% by weight of pentachlorophenyl allyl carbonate and, as a 6 carrier therefor, a mineral oil consisting predominately of hydrocarbons containing 10 to 20 carbon atoms.

2. A herbicidal composition comprising as an essential active ingredient 0.1% to 10% by weight of pentachlorophenyl ethyl carbonate and, as a carrier therefor, a mineral oil consisting predominately of hydrocarbons containing 10 to 20carbon atoms. 7

3. A herbicidal composition comprising as an essential active ingredient 0.1% to 10% by weight of pentachlorophenyl allyl carbonate and, as a carrier therefor, a mineral oil consisting predominately of hydrocarbons containing 10 to 20 carbon atoms, water and a surface-active agent. I

4. A herbicidal composition comprising as an essential active ingredient 0.1% to 10% by weight of pentachlorophenyl ethyl carbonate and, as a carrier therefor, a mineral oil consisting predominately of hydrocarbons containing 10 to 20 carbon atoms, water and a surfaceactive agent.

5. Aherbicidal composition comprising as an essential active ingredient 0.1 to 10% by weight of an active herbicidal ingredient selected from the class consisting of alkyl and alkenyl pentachlorophenyl carbonates, and, as a carrier therefor, a mineral oil consisting predominately of hydrocarbons containing 10 to 20 carbon atoms.

6. A herbicidal composition comprising as an essential active herbicidal ingredient 0.1 to 10% by weight of an active herbicide ingredient selected from the class consisting of alkyl and alkenyl phentachlorophenyl carbonates. and, as a carrier therefor, a mineral oil consisting predominately of hydrocarbons containing 10 to 20 carbon atoms, water and a surface-active agent.

LUTHER L. BAUMGARTNER.

REFERENCES CITED The following references are of record in the file of this patent:

UNITED STATES PATENTS Name Date Jones Mar. 12, 1946 OTHER REFERENCES Number 

5. A HERBICIDAL COMPOSITION COMPRISING AS AN ESSENTIAL ACTIVE INGREDINET 0.1 TO 10% BY WEIGHT OF AN ACTIVE HERBICIDAL INGREDIENT SELECTED FROM THE CLASS CONSISTING OF ALKYL AND ALKENYL PENTACHLOROPHENYL CARBONATES, AND, AS A CARRIER THEREFOR, A MINERAL OIL CONSISTING PREDOMINATELY OF HYDROCARBONS CONTAINING 10 TO 20 CARBON ATOMS. 